Synthesis of Glycyrol

C21H18O6

Principal investigator	Hak Sung Kim
Publication year	2008
Synthesis type	Total
Number of steps	12 (3 parts)
References	Tetrahedron Lett. 2008, 49, 6835.

Part 1 of 3

i-Pr2NEt, MeOCH2Cl

CH2Cl2

0 °C, 60 min

K2CO3, Me2SO4

Acetone

80 °C, 60 min, 90% (2 steps)

See the Williamson Ether Synthesis

MeOH

RT, 2 h, 66%

K2CO3

Acetone

Reflux, 8 h, 66%

See the Williamson Ether Synthesis

								
																	PhNEt2															

								Reflux, 								60 min, 								64%
							
								See the Claisen Rearrangement
							
								See the Cope Rearrangement

NaH, EtOCO2Et

0 °C to Reflux, 5 h, 68%

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Part 2 of 3

BnBr, K2CO3

Acetone

RT, 6 h, 95%

See the Williamson Ether Synthesis

NaBO3.4H2O

AcOH

40-45 °C, 8.5 h, 100%

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Part 3 of 3

Na2CO3

H2O

RT, 2.5 h

DMF

Reflux, 60 min, 87% (2 steps)

See the Smiles Rearrangement

Et3N, Pd(OAc)2

PhMe

Reflux, 6 h, 87%

See the Mizoroki-Heck Reaction

AlCl3

CH2Cl2, PhNMe2

0 to 50 °C, 30 min, 68%

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