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A solution of 73 g. (0.5 m) of 5,8-dihydro-1-naphthol in 100 ml. DMSO is treated with 0.5 m sodium methoxide. The mixture is cooled in an ice bath and treated dropwise with 0.5 mole benzyl bromide with shaking periodically. The mixture is gradually allowed to warm up to about 45° toward the end of addition. The mixture is stirred 3 hrs. longer, then poured into 1 liter H2O and extracted into ether. Extracts are washed twice with 10% NaOH, dried, taken to dryness leaving almost a quantitative yield of crystalline 5,8-dihydro-1-naphthyl benzyl ether.

1. temperatureThe mixture is cooled in an ice bath
2. temperatureto warm up to about 45° toward the end of addition
3. stirringThe mixture is stirred 3 hrs
4. extractionextracted into ether
5. washExtracts are washed twice with 10% NaOH
6. customdried